Thanks for the tips. I think I'm going to go with Momo Winter 2 16" with Blizzak WS70 tires. I saw a deal at discounttire with that package for $900, which I think is decent.

At what point in the season must you switch over to winter tires? I've heard that when temps drop below 40 degrees consistently, but others say not until you think it'll start snowing.

The main issue is what temperature the rubber compound of each tire is designed to do, so temp is a better indicator. The rubber compound in Summer tires begins to "chunk" off in the 40's, while the rubber in winters gets a little greasy in the 50's and above. Driving on any tire outside of it's designed temperature range will, at best, reduce the life of the tire, and at worst, reduce the life of it's owner.